Names
IUPAC name
3,3′,4′,5,7,8-Hexahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H -1-benzopyran-4-one
Other names
Articulatidin Equisporol 3,5,7,8,3',4'-Hexahydroxyflavone
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
N Key: YRRAGUMVDQQZIY-UHFFFAOYSA-N
N InChI=1/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
Key: YRRAGUMVDQQZIY-UHFFFAOYAI
C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O
Properties
C15 H10 O8
Molar mass
318.23 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Gossypetin , also known as 3,5,7,8,3',4'-hexahydroxyflavone , is a flavonol , a type of flavonoid . It has been isolated from the flowers and the calyx of Hibiscus sabdariffa (roselle) and exhibits a strong antibacterial activity.[1] [2] The compound has also been found to act as an antagonist of TrkB .[3] Recently it was shown that gossypetin has radioprotective activity.[citation needed ]
The enzyme 8-hydroxyquercetin 8-O -methyltransferase uses S -adenosyl methionine and gossypetin to produce S -adenosylhomocysteine and 3,5,7,3',4'-pentahydroxy-8-methoxyflavone.[citation needed ]
In 2022, a study in an animal model using intragastric administration suggested that the flavonoid gossypetin facilitated the clearance of beta-amyloid in the brain and is a promising target for the study of treatments for Alzheimer's Disease by enhancing microglial phagocytic activity against Aβ.[4]
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Periodic trends in Periodic Table
See also
References
^ Antibacterial activity of gossypetin isolated from hibiscus sabdariffa
^ Amitava Khan, Krishnendu Manna, Chinchubose, Mahuya Sinha, Dipesh Kr Das, Swaraj Bandhu Kesh, Anindita Chakrabarty, Asoke Banerji & Sanjit Dey: Gossypetin, a naturally occurring hexahydroxy flavones ameliorates gamma radiation mediated DNA damage International Journal of Radiation Biology (2013):89(11): 965-975.
^ Obianyo, Obiamaka; Ye, Keqiang (2013). "Novel small molecule activators of the Trk family of receptor tyrosine kinases" . Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics . 1834 (10): 2213–2218. doi :10.1016/j.bbapap.2012.08.021 . ISSN 1570-9639 . PMC 3602283 . PMID 22982231 .
^ Jo, K.W., Lee, D., Cha, D.G. et al., Gossypetin ameliorates 5xFAD spatial learning and memory through enhanced phagocytosis against Aβ , Alzheimer's Research & Therapy, October 21, 2022 - Alz Res Therapy 14, 158 (2022)
Flavonols and their conjugates
Backbone
Flavonols
Aglycones Conjugates
Glycosides of herbacetin Glycosides of kaempferol
Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)
Glycosides of myricetin Conjugates of quercetin
O -Methylated flavonols
Aglycones Glycosides
of isorhamnetin
Narcissin (Isorhamnetin 3-O-rutinoside)
Isorhamnetin 3-O-glucoside
Tamarixetin 7-rutinoside
other
Azalein (Azaleatin 3-O-α-L-rhamnoside)
Centaurein (Centaureidin 7-O-glucoside)
Eupalin (Eupalitin 3-0-rhamnoside)
Eupatolin (Eupatolitin 3-O-rhamnoside)
Jacein (Jaceidin 7-O-glucoside)
Patulitrin (Patuletin 7-O-glucoside
Xanthorhamnin (Rhamnetin glycoside)
Derivative flavonols
Aglycones
Noricaritin
Dihydronoricaritin
Glycosides
Pyranoflavonols
Furanoflavonols
Semisynthetic
Angiopoietin
Kinase inhibitors: Altiratinib
CE-245677
Rebastinib
CNTF EGF (ErbB)
FGF
FGFR1 FGFR2
Agonists: Ersofermin
FGF (1 , 2 (bFGF) , 3 , 4 , 5 , 6 , 7 (KGF ), 8 , 9 , 10 (KGF2) , 17 , 18 , 22 )
Palifermin
Repifermin
Selpercatinib
Sprifermin
Trafermin
Antibodies: Aprutumab
Aprutumab ixadotin
FGFR3 FGFR4 Unsorted
HGF (c-Met) IGF
IGF-1
Kinase inhibitors: BMS-754807
Linsitinib
NVP-ADW742
NVP-AEW541
OSl-906
IGF-2
Antibodies: Dusigitumab
Xentuzumab (against IGF-1 and IGF-2)
Others
Cleavage products/derivatives with unknown target: Glypromate (GPE, (1-3)IGF-1)
Trofinetide
LNGF (p75NTR )
Aptamers: Against NGF: RBM-004
Decoy receptors: LEVI-04 (p75<sup>NTR</sup>-Fc)
PDGF RET (GFL)
SCF (c-Kit) TGFβ Trk
TrkA
Negative allosteric modulators: VM-902A
Aptamers: Against NGF: RBM-004
Decoy receptors: ReN-1820 (TrkAd5)
TrkB
Agonists: 3,7-DHF
3,7,8,2'-THF
4'-DMA-7,8-DHF
7,3'-DHF
7,8-DHF
7,8,2'-THF
7,8,3'-THF
Amitriptyline
BDNF
BNN-20
Deoxygedunin
Deprenyl
Diosmetin
DMAQ-B1
HIOC
LM22A-4
N-Acetylserotonin
NT-3
NT-4
Norwogonin (5,7,8-THF)
R7
R13
TDP6
TrkC
VEGF Others
Additional growth factors: Adrenomedullin
Colony-stimulating factors (see here instead)
Connective tissue growth factor (CTGF)
Ephrins (A1 , A2 , A3 , A4 , A5 , B1 , B2 , B3 )
Erythropoietin (see here instead)
Glucose-6-phosphate isomerase (GPI; PGI, PHI, AMF)
Glia maturation factor (GMF)
Hepatoma-derived growth factor (HDGF)
Interleukins /T-cell growth factors (see here instead)
Leukemia inhibitory factor (LIF)
Macrophage-stimulating protein (MSP; HLP, HGFLP)
Midkine (NEGF2)
Migration-stimulating factor (MSF; PRG4)
Oncomodulin
Pituitary adenylate cyclase-activating peptide (PACAP)
Pleiotrophin
Renalase
Thrombopoietin (see here instead)
Wnt signaling proteins
Additional growth factor receptor modulators: Cerebrolysin (neurotrophin mixture)
This page was last edited on 2 May 2023, at 16:11